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1
Make the filling and frosting: place the pudding mix and milk in a 2-qt saucepan over medium-high heat. Whisk constantly until the mixture comes to a boil and thickens, 4-5 minutes. Turn off the heat.
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2
Add the chocolate chips, butter, and vanilla and stir until the chips and butter melts, 2 minutes.
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3
Remove the pan from the heat and cover the pudding with plastic wrap placed directly on its surface. Let cool for 45 minutes at room temperature.
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4
Meanwhile, preheat the oven to 350u00b0F Line 24 cupcake wells with paper liners.
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5
Make the batter: place the cake mix, cocoa powder, buttermilk, oil, eggs, and vanilla in a large mixing bowl. Blend with an electric mixer on low speed for 30 seconds.
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6
Stop the mixer and scrape down the sides of the bowl. Increase the mixer speed to medium and beat 2 minutes more. Batter will be thick.
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7
Scoop 1/4 cup batter into each cupcake well~you should get 24.
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8
Bake for 17-20 minutes, until tops are springy when lightly pressed. Cool in the pans on wire racks for 5 minutes.
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9
Remove 4 cupcakes from the pans and crumble them into a bowl, making coarse crumbs.
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10
Loosen the remaining cupcakes from the pans and cool them on wire racks for 15 minutes.
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11
Divide the pudding mixture into 2 portions. Fit a pastry bag with a large round tip and spoon 1 cup of the filling into the bag. Gently push the tip into the center of each cupcake and squirt a generous amount of pudding inside. Refill the bag as needed and repeat for all 20 cakes.
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12
Place a heaping tablespoons of the remaining pudding portion on the top of each cupcake and spread to cover the entire surface. Top the frosting with a sprinkling of cupcake crumbs, pressing down slightly so they stick.
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13
Store uneaten cupcakes covered in the refrigerator for up to 5 days.
